Are You Charging Too Little… On Purpose?

Are You Charging Too Little… On Purpose?

Author: Millo June 5, 2026 Duration: 20:10
Adam Barta's design agency just signed five clients in three days — and now he's wondering if it's time to raise his prices. The momentum is real, but so is the fear of charging too much and watching it all fall apart. Preston and guest co-host AJ Cassata from Revenue Boost walk through the art and science of pricing: how to test your limits incrementally, why a high close rate is actually a red flag, and how to start building agency-level pricing into your business before you ever hire your first employee. Links: Support our show sponsors -> ⁠https://freelancetofounder.com/sponsors⁠ Submit your own question -> ⁠https://freelancetofounder.com/ask Attend The "10X Your Freelancing" Summit -> https://10XFreelance.com (FREE) Learn more about your ad choices. Visit megaphone.fm/adchoices

There’s a common gap between working for yourself and truly building something that lasts, and Freelance to Founder lives in that space. This isn’t just theory; it’s a daily conversation for freelancers who are tired of the unpredictable income and ready to create a real business. Host Preston Lee draws from his own journey from freelancer to someone who has built and sold companies, and he brings that grounded perspective to every episode. Nearly every weekday, Preston is joined by other founders and entrepreneurs who’ve navigated the same path, breaking down the practical steps you can take to scale your solo operation. The call-in format means you’re hearing real questions from people in the trenches, facing the same client issues, pricing dilemmas, and growth plateaus you might be. Listening to this podcast feels like having a direct line to a supportive and experienced mastermind group, one that focuses on actionable strategies over vague inspiration. It’s for the designer, writer, developer, or consultant who’s ready to move beyond the feast-or-famine cycle and lay the foundation for something more substantial and sustainable. The discussions are candid, the advice is tested, and the goal is always clear: helping you transition from a solo practitioner to the founder of a thriving business.
Author: Language: English Episodes: 100

Freelance to Founder
Podcast Episodes
Burned in the Past & Scared to Hire [not-audio_url] [/not-audio_url]

Duration: 18:04
When bad contractor experiences leave you gun-shy about hiring, how do you rebuild trust and create a successful team? Emily's struggle with past hiring mishaps is a common challenge for freelancers and agency owners. In…
You've Got to Stop Doing Everything [not-audio_url] [/not-audio_url]

Duration: 19:15
Mark is stuck in the freelance grind—working nonstop and wondering how to transform his solo operation into a real company. Preston Lee and Kevin Rice dive deep into the critical moment when freelancers must shift from d…
Is Work-Life Balance a Myth? [not-audio_url] [/not-audio_url]

Duration: 21:25
Kevin Rice knows the delicate dance of entrepreneurship and fatherhood all too well. After scaling his digital agency to a nine-figure exit, he discovered the hard truth that success means nothing if it comes at the cost…
Can You Break the 7-Figure Barrier? [not-audio_url] [/not-audio_url]

Duration: 34:22
Michael is standing at a critical crossroads in his entrepreneurial journey—desperate to break through the seven-figure barrier but unsure how to transform his current six-figure business into something truly scalable. I…
Trouble "Turning Off" Your Brain? [not-audio_url] [/not-audio_url]

Duration: 14:17
Jordan is struggling with the modern remote work challenge—feeling like his brain never fully switches off. Preston and Steven dive deep into practical strategies for creating mental boundaries, exploring how freelancers…
The Power of Delegation [not-audio_url] [/not-audio_url]

Duration: 19:32
Anthony is standing at a critical crossroads in his entrepreneurial journey—he's just hired his first two teammates and is wrestling with the most fundamental leadership challenge: how to spend his time effectively. Pres…
When Your Business is "Meh" [not-audio_url] [/not-audio_url]

Duration: 16:52
Ethan has been hustling for three years, but feels stuck in a business that's just "meh". Preston Lee and Steven Puri dive deep into the critical strategies for transforming a stagnant freelance business into a thriving…
Most People Get This Wrong When It Comes to Hiring [not-audio_url] [/not-audio_url]

Duration: 20:04
Omar is standing at a critical crossroads in his business, wrestling with a fundamental hiring decision that could shape his team's future. Should he bring on a jack-of-all-trades virtual assistant who can handle multipl…
Why You're Scared to Hire a VA (& How to Overcome It) [not-audio_url] [/not-audio_url]

Duration: 15:00
Melissa is standing at a critical crossroads in her freelance business—overwhelmed by workload but paralyzed by the fear of delegation. Preston and Joey Vitale dive deep into the art of hiring your first virtual assistan…
How to Hire w/out Losing Control [not-audio_url] [/not-audio_url]

Duration: 17:52
Keisha's agency is at a critical turning point. As her business grows, she's wrestling with the ultimate entrepreneurial challenge: how to build a team without losing control or compromising quality. Preston Lee and Joey…